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{{Short description|Chemical compound}} {{Redirect|DMT}} {{About|N,N-dimethyltryptamine|other dimethyltryptamines|Dimethyltryptamine (disambiguation)}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | verifiedrevid = 623685269 | Watchedfields = changed | drug_name = Dimethyltryptamine (DMT) | image = DMT.svg | image_class = skin-invert-image | width = 200 | image2 = Dimethyltryptamine molecule ball.png | image_class2 = bg-transparenT | width2 = 170 <!--Physiological data-->| receptors = At least 13 receptors (e.g., serotonin, sigma, trace amine-associated) | precursor = [[Tryptophan]] | source_tissues = [[Central nervous system]] (exact source tissues are not fully established) | target_tissues = Central nervous system <!--Clinical data-->| routes_of_administration = [[Oral administration|By mouth]] (usually with an {{Abbrlink|MAOI|monoamine oxidase inhibitor}}), [[inhalation]], [[insufflation]], [[rectal (medicine)|rectal]], [[Intramuscular injection|intramuscular]], [[intravenous injection|intravenous]]<ref name="CameronOlson2018" /><ref name="CarbonaroGatch2016" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /><ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> | class = [[Serotonergic psychedelic]] ([[hallucinogen]])<ref name="CameronOlson2018" /><ref name="CarbonaroGatch2016" /><ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> <!--Legal status-->| legal_AU = S9 | legal_CA = Schedule III | legal_UK = Class A | legal_US = Schedule I | legal_DE = Anlage I | legal_BR = F2 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref> | legal_UN = P I <!--Pharmacokinetic data-->| bioavailability = Very low and inactive (except with an {{Abbrlink|MAOI|monoamine oxidase inhibitor}})<ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> | protein_bound = | metabolism = [[Oxidative deamination]] ({{Abbrlink|MAO-A|Monoamine oxidase A}}), ''N''-[[oxidation]], ''N''-[[demethylation]], [[peroxidation]]<ref name="CameronOlson2018" /><ref name="CarbonaroGatch2016" /> | metabolites = * [[Indole-3-acetic acid]] (NMT) (63–97%)<ref name="CameronOlson2018" /><ref name="CarbonaroGatch2016" /><ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> * [[Dimethyltryptamine-N-oxide|DMT-''N''-oxide]] (DMT-NO) (3–28%)<ref name="CameronOlson2018" /><ref name="CarbonaroGatch2016" /><ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> * [[N-Methyltryptamine|''N''-Methyltryptamine]]<ref name="CarbonaroGatch2016" /> * [[Tryptamine]]<ref name="CameronOlson2018" /> * Others<ref name="CameronOlson2018" /> | onset = * [[Inhalation]]: 10–15 seconds<ref name="Brito-da-CostaDias-da-SilvaGomes2020" /><ref name="CameronOlson2018" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /> * [[Intravenous]]: ≤2–5 min<ref name="CameronOlson2018" /> * [[Intramuscular injection|Intramuscular]]: 2–5{{nbsp}}min<ref name="CarbonaroGatch2016" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /> * [[Oral administration|Oral]] with {{Abbrlink|MAOI|monoamine oxidase inhibitor}}: ≤1{{nbsp}}hour<ref name="CarbonaroGatch2016" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /> | elimination_half-life = * Alone: 5–15{{nbsp}}min<ref name="CameronOlson2018" /><ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> * With an {{Abbrlink|MAOI|monoamine oxidase inhibitor}}: 1–4{{nbsp}}hours<ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> | duration_of_action = * [[Inhalation]]: ≤30{{nbsp}}min<ref name="CarbonaroGatch2016" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /> * [[Intravenous]]: ≤30{{nbsp}}min<ref name="RodriguesAlmeidaVieira-Coelho2019" /><ref name="Barker2022">{{cite journal | vauthors = Barker SA | title = Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT | journal = Psychopharmacology (Berl) | volume = 239 | issue = 6 | pages = 1749–1763 | date = June 2022 | pmid = 35064294 | pmc = 8782705 | doi = 10.1007/s00213-022-06065-0 | url = }}</ref> * [[Intramuscular injection|Intramuscular]]: 30–60{{nbsp}}min<ref name="CarbonaroGatch2016" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /> * [[Oral administration|Oral]] with {{Abbrlink|MAOI|monoamine oxidase inhibitor}}: 4–6{{nbsp}}hours<ref name="CarbonaroGatch2016" /><ref name="RodriguesAlmeidaVieira-Coelho2019" /><ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> | excretion = [[Urine]]<ref name="Brito-da-CostaDias-da-SilvaGomes2020" /> <!--Identifiers-->| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 61-50-7 | ATC_prefix = None | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01488 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = WUB601BHAA | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28969 | PubChem = 6089 | IUPHAR_ligand = 141 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5864 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C08302 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 12420 | PDB_ligand = A1AFV | synonyms = Dimethyltryptamine; DMT; ''N'',''N''-DMT <!--Chemical data-->| IUPAC_name = 2-(1''H''-Indol-3-yl)-''N'',''N''-dimethylethanamine | C = 12 | H = 16 | N = 2 | SMILES = CN(CCC1=CNC2=C1C=CC=C2)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DMULVCHRPCFFGV-UHFFFAOYSA-N <!--Physical data-->| density = 1.099 | melting_point = 40 | boiling_point = 160 | boiling_notes = at {{convert|0.6|Torr|Pa|abbr=on}}<ref>{{Cite journal |title=Untersuchungen zur Trifluoracetylierung der Methylderivate von Tryptamin und Serotonin mit verschiedenen Derivatisierungsreagentien: Synthesen, Spektroskopie sowie analytische Trennungen mittels Kapillar-GC |trans-title=Trifluoracetylation of methylated derivatives of tryptamine and serotonin by different reagents: synthesis, spectroscopic characterizations, and separations by capillary gas chromatography |year=1999 |journal=Zeitschrift für Naturforschung B |volume=54 |issue=3 |pages=397–414 | vauthors = Häfelinger G, Nimtz M, Horstmann V, Benz T |doi=10.1515/znb-1999-0319 |s2cid=101000504 }}</ref><br />also reported as<br />{{convert|80|-|135|C}} at {{convert|0.03|Torr|Pa|abbr=on}}<ref>{{cite journal | vauthors = Corothie E, Nakano T | title = Constituents of the bark of Virola sebifera | journal = Planta Medica | volume = 17 | issue = 2 | pages = 184–188 | date = May 1969 | pmid = 5792479 | doi = 10.1055/s-0028-1099844 | bibcode = 1969PlMed..17..184C | s2cid = 43312376 }}</ref> }} {{Psychedelic sidebar}} '''Dimethyltryptamine''' ('''DMT'''), also known as '''''N'',''N''-dimethyltryptamine''' ('''''N'',''N''-DMT'''), is a [[Psychedelic drug|serotonergic hallucinogen]] and [[Investigational New Drug|investigational drug]] of the [[substituted tryptamine|tryptamine]] family that [[natural product|occurs naturally]] in many plants and animals, including humans.<ref name="CameronOlson2018">{{cite journal | vauthors = Cameron LP, Olson DE | title = Dark Classics in Chemical Neuroscience: N, N-Dimethyltryptamine (DMT) | journal = ACS Chem Neurosci | volume = 9 | issue = 10 | pages = 2344–2357 | date = October 2018 | pmid = 30036036 | doi = 10.1021/acschemneuro.8b00101 | url = }}</ref><ref name="CarbonaroGatch2016">{{cite journal | vauthors = Carbonaro TM, Gatch MB | title = Neuropharmacology of ''N'',''N''-dimethyltryptamine | journal = Brain Research Bulletin | volume = 126 | issue = Pt 1 | pages = 74–88 | date = September 2016 | pmid = 27126737 | pmc = 5048497 | doi = 10.1016/j.brainresbull.2016.04.016 }}</ref><ref name="RodriguesAlmeidaVieira-Coelho2019">{{cite journal | vauthors = Rodrigues AV, Almeida FJ, Vieira-Coelho MA | title = Dimethyltryptamine: Endogenous Role and Therapeutic Potential | journal = J Psychoactive Drugs | volume = 51 | issue = 4 | pages = 299–310 | date = 2019 | pmid = 31018803 | doi = 10.1080/02791072.2019.1602291 | hdl = 10216/114373 | url = | hdl-access = free }}</ref><ref>{{Cite web | work = PubChem | publisher = U.S. National Library of Medicine |title=Dimethyltryptamine |url=https://pubchem.ncbi.nlm.nih.gov/compound/Dimethyltryptamine |access-date=2025-05-22 |language=en}}</ref> DMT is used as a [[psychedelic drug]] and prepared by various cultures for [[ritual]] purposes as an [[entheogen]].<ref name="McKennaTowers1984">{{cite journal | vauthors = McKenna DJ, Towers GH, Abbott F | title = Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and beta-carboline constituents of ayahuasca | journal = Journal of Ethnopharmacology | volume = 10 | issue = 2 | pages = 195–223 | date = April 1984 | pmid = 6587171 | doi = 10.1016/0378-8741(84)90003-5 }}</ref> DMT has a rapid [[onset of action|onset]], intense effects, and a relatively short [[duration of action]]. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a [[psychedelic experience]] in considerably less time than with other substances such as [[Lysergic acid diethylamide|LSD]] or [[psilocybin mushroom]]s.<ref>{{cite journal | vauthors = Haroz R, Greenberg MI | title = Emerging drugs of abuse | journal = The Medical Clinics of North America | volume = 89 | issue = 6 | pages = 1259–1276 | date = November 2005 | pmid = 16227062 | doi = 10.1016/j.mcna.2005.06.008 | oclc = 610327022 }}</ref> DMT can be inhaled or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last about five to fifteen minutes. Effects can last three hours or more when orally ingested along with a [[monoamine oxidase inhibitor]] (MAOI), such as the [[Ayahuasca|ayahuasca brew]] of many native [[Amazon rainforest|Amazonian]] tribes.<ref name="Pickover 2005">{{cite book |title=Sex, Drugs, Einstein, and Elves: Sushi, Psychedelics, Parallel Universes, and the Quest for Transcendence | vauthors = Pickover C |year=2005 |publisher=Smart Publications |isbn=978-1-890572-17-4 |url=https://archive.org/details/sexdrugseinstein00clif }}</ref> DMT induces intense, often indescribable subjective experiences involving vivid visual hallucinations, altered [[Perception|sensory perception]], [[Ego death|ego dissolution]], and encounters with seemingly autonomous entities. DMT is generally considered non-addictive with low dependence and no tolerance buildup, but it may cause acute psychological distress or [[Circulatory system|cardiovascular]] effects, especially in predisposed individuals. DMT was first synthesized in 1931. It is a [[functional analog (chemistry)|functional analog]] and [[structural analog]] of other psychedelic tryptamines such as [[O-acetylpsilocin|''O''-acetylpsilocin]] (4-AcO-DMT),<ref>{{cite journal | vauthors = Jones NT, Wagner L, Hahn MC, Scarlett CO, Wenthur CJ | title = <i>In vivo</i> validation of psilacetin as a prodrug yielding modestly lower peripheral psilocin exposure than psilocybin | language = English | journal = Frontiers in Psychiatry | volume = 14 | page = 1303365 | date = 2024-01-08 | pmid = 38264637 | doi = 10.3389/fpsyt.2023.1303365 | doi-access = free | pmc = 10804612 }}</ref> [[psilocybin]] (4-PO-DMT), [[psilocin]] (4-HO-DMT), [[NB-DMT]], [[5-MeO-DMT|''O''-methylbufotenin]] (5-MeO-DMT), and [[bufotenin]] (5-HO-DMT). Parts of the structure of DMT occur within some important biomolecules like [[serotonin]] and [[melatonin]], making them structural analogs of DMT. DMT exhibits broad and variable [[Ligand (biochemistry)|binding affinities]] across numerous receptors, showing its strongest interactions with serotonin receptors, especially [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[5-HT1A receptor|5-HT<sub>1A</sub>]], and [[5-HT2C receptor|5-HT<sub>2C</sub>]], which are believed to mediate its psychedelic effects. [[Endogeny (biology)|Endogenous]] DMT, a psychedelic compound, is naturally produced in mammals including humans, with evidence showing its synthesis and presence in brain and body tissues, though its exact roles and origins, especially in the [[pineal gland]], remain debated. DMT is internationally illegal without authorization, with most countries banning its possession and trade, though some allow religious use of ayahuasca, a DMT-containing [[decoction]]. Short-acting psychedelics like DMT are considered [[Scalability|scalable]] alternatives to [[psilocybin]]; {{cns|date=May 2025|DMT is currently undergoing clinical trials for treatment-resistant depression.}} {{TOC limit}}
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